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9-benzyl naphthylamine and synthesis method thereof

A technology of benzylnaphthylamine and its synthesis method, which is applied in the field of organic synthesis, can solve the problems of cumbersome synthesis route of benzylnaphthylamine, difficulty in accurate positioning, and many by-products, and achieve expansion of imagination space, strong positioning effect, and simple steps Effect

Active Publication Date: 2019-05-24
YULIN NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, in the existing methods, using anthracene as a substrate to react to generate benzylnaphthylamine has cumbersome synthetic routes, many by-products, low yield, and it is difficult to accurately locate the No. 9 position of anthracene. insurmountable technical problems

Method used

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  • 9-benzyl naphthylamine and synthesis method thereof
  • 9-benzyl naphthylamine and synthesis method thereof
  • 9-benzyl naphthylamine and synthesis method thereof

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Embodiment 1

[0028] Step 1: Dissolve (2mmol, 356mg) anthracene in 10mL dichloromethane, cool down to 0°C, add (2mmol, 230mg) 1,1-dichloromethyl ether and 390mg titanium tetrachloride, warm up to room temperature, stir for 2 -5h, add 20mL of saturated sodium bicarbonate, extract with 20mL of dichloromethane to obtain an organic phase and dry it, evaporate the solvent under reduced pressure to obtain intermediate S1, namely 9-formylnaphthalene. As a yellow solid, the yield is 95%. m.p:135.1-136.0℃. 1 H NMR (400MHz, CDCl 3 )δ11.5(s,1H),8.97(dd,J=9.0,0.8Hz,2H),8.67(s,1H),8.05(d,J=8.5Hz,2H),7.70-7.65(m,2H ),7.61-7.47(m,2H)ppm; 13 C NMR (100MHz, CDCl 3 )δ193.0, 135.2, 132.1, 131.1, 129.3, 129.1, 125.7, 124.7, 123.5ppm; Intermediate S1 1 See the H NMR chart for details figure 2 , 13 See the C NMR chart for details image 3 .

[0029] Step 2: Intermediate S1 (2mmol, 412mg) and (2mmol, 234mg) tert-butyl carbamate obtained in step 1 were dissolved in a mixed solvent (10mL) of acetonitrile ...

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Abstract

The invention discloses 9-benzyl naphthylamine with mild reaction conditions, good atom economy and high yield and a synthesis method of the 9-benzyl naphthylamine. The synthesis method comprises thefollowing steps: dissolving anthracene in dichloromethane, cooling to the temperature of 0 DEG C, adding 1, 1-dichloromethyl ether and titanium tetrachloride, heating to the room temperature, stirring, adding saturated sodium bicarbonate, extracting with dichloromethane to obtain an organic phase, drying, evaporating a solvent under reduced pressure, dissolving tert-butyl carbamate in a mixed solvent of acetonitrile and the dichloromethane, stirring, adding triethylsilane and trifluoroacetic acid, and reacting at room temperature; adding saturated sodium bicarbonate, extracting with dichloromethane to obtain an organic phase, drying, evaporating the solvent under reduced pressure, dissolving in the dichloromethane, adding trifluoroacetic acid, stirring, evaporating the solvent until a solid is obtained, adding the solid in sodium hydroxide, stirring, adding dichloromethane for extraction, drying the obtained organic phase, evaporating the solvent until a solid is obtained so as to obtain the target product.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a 9-benzylnaphthylamine and a synthesis method thereof. Background technique [0002] Anthracene, also called scintillation crystal, a condensed ring aromatic hydrocarbon with three rings, molecular formula C1 4 h 10 , a triphenyl ring composed of solid polycyclic aromatic hydrocarbons. It exists in coal tar, and the centers of the three rings of anthracene are on a straight line, which is the isomer of phenanthrene. Anthracene is a colorless flaky crystal with blue-purple fluorescence, melting point 215°C, boiling point 340°C, relative density 1.283 (25 / 4°C); easily sublimated, insoluble in water, hardly soluble in ethanol and ether, easily soluble in hot benzene , the chemical activity of the 9 and 10 positions in the anthracene molecule is relatively high. [0003] However, in the existing methods, using anthracene as a substrate to react to generate benzylnaphthylamine ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/31C07C209/24C07C47/546C07C45/00
Inventor 李秀英黄国保罗金荣韦贤生黄瑞标景亮
Owner YULIN NORMAL UNIVERSITY
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